Toast CRO exercises options, sells 14K shares
Rhea-AI Filing Summary
Toast, Inc. (TOST) reported that Chief Revenue Officer Jonathan Vassil exercised options for 14,280 shares of Class A Common Stock at an exercise price of $2.21 per share on September 2, 2026, and sold the same number of shares in open-market transactions pursuant to a Rule 10b5-1 trading plan. Following the option exercise, he held 285,871 stock options directly and 84,269 shares indirectly through The Jonathan S. Vassil Grantor Retained Annuity Trust #1.
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Insider Trade Summary 10b5-1
Exercise and Sale: 14,280 shares ($452K approx. pre-tax spread)
Exercise and Sale
5 txns
Insider
Vassil Jonathan
Role
Chief Revenue Officer
Sold
14,280 shs ($484K)
Approx. gross sale proceeds
$484K
Approx. exercise cost
$32K
Approx. pre-tax spread
$452K
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Stock Option (Right to Buy) F1, F4 | 14,280 | $0.00 | $0.00 |
| Exercise | Class A Common Stock F1 | 14,280 | $2.21 | $32K |
| Sale | Class A Common Stock F1, F2 | 5,100 | $33.542 | $171K |
| Sale | Class A Common Stock F1, F3 | 9,180 | $34.095 | $313K |
| holding | Class A Common Stock | -- | -- | -- |
Holdings After Transaction:
Stock Option (Right to Buy) — 285,871 contracts (Direct);
Class A Common Stock — 69,966 shares (Direct);
Class A Common Stock — 84,269 shares (Indirect, The Jonathan S. Vassil Grantor Retained Annuity Trust #1)
Footnotes (4)
- F1. This transaction was effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on March 13, 2026.
- F2. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $32.945 to $33.940 inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the Staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within this price range set forth in this footnote.
- F3. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $33.95 to $34.26 inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the Staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within this price range set forth in this footnote.
- F4. The shares subject to this option are fully vested and exercisable as of the date hereof.
Key Figures
Options exercised: 14,280 shares
Option exercise price: $2.21 per share
Shares sold (first block): 5,100 shares at $33.542
+4 more
7 metrics
Options exercised
14,280 shares
Stock options converted into Class A Common Stock on September 2, 2026
Option exercise price
$2.21 per share
Exercise price for 14,280 stock options into Class A Common Stock
Shares sold (first block)
5,100 shares at $33.542
Weighted average sale price; trades ranged from $32.945 to $33.940
Shares sold (second block)
9,180 shares at $34.095
Weighted average sale price; trades ranged from $33.95 to $34.26
Options held after transaction
285,871 options
Directly held stock options following the reported exercise
Indirect common shares held
84,269 shares
Class A Common Stock held through The Jonathan S. Vassil Grantor Retained Annuity Trust #1
Rule 10b5-1 plan adoption date
March 13, 2026
Date Vassil adopted the trading plan governing these transactions
Key Terms
Rule 10b5-1 trading plan, weighted average price, Grantor Retained Annuity Trust, Class A Common Stock
4 terms
Rule 10b5-1 trading plan regulatory
"transaction was effected pursuant to a Rule 10b5-1 trading plan"
A Rule 10b5-1 trading plan is a pre-arranged schedule that allows company insiders to buy or sell stock at specific times, even if they have inside information. It helps prevent accusations of unfair trading by making these transactions look planned and transparent, rather than sneaky or illegal.
weighted average price financial
"The reported price in Column 4 is a weighted average price"
Weighted average price is the average price of a security where each trade or component is counted according to its size, so bigger trades pull the average more than smaller ones. Think of it like calculating the average cost of a grocery haul where items you bought more of have greater influence on the final per-item cost. Investors use it to understand the true average price paid or received, judge execution quality, and compare trading performance against market movement.
Grantor Retained Annuity Trust financial
"The Jonathan S. Vassil Grantor Retained Annuity Trust #1"
A grantor retained annuity trust (GRAT) is an estate-planning tool where the person who creates the trust transfers assets into it but receives fixed cash payments (an annuity) from the trust for a set number of years; whatever remains after that term passes to designated beneficiaries. It matters to investors because it can shift future appreciation of assets out of the creator’s taxable estate—like putting an asset into a timed vending machine that pays you fixed amounts while any extra value that grows inside the machine goes to heirs with reduced gift or estate tax consequences.
Class A Common Stock financial
"underlying security title is Class A Common Stock"
Class A common stock is a category of a company’s shares that carries a specific set of ownership rights—most commonly defined voting power and claims on dividends—set out in the company’s charter. For investors it matters because the class determines how much influence you have over corporate decisions, the share’s likely dividend and trading behavior, and how it compares in value to other share classes, like choosing a particular seat with different privileges at the company’s decision-making table.
FAQ
What insider transactions did Toast, Inc. (TOST) report for Jonathan Vassil?
Toast reported that Chief Revenue Officer Jonathan Vassil exercised 14,280 stock options for Class A Common Stock at $2.21 per share on September 2, 2026, and sold 14,280 shares of Class A Common Stock in open-market transactions the same day.
Were Jonathan Vassil’s Toast (TOST) transactions under a Rule 10b5-1 plan?
Yes. The filing states that the reported transactions were effected pursuant to a Rule 10b5-1 trading plan adopted by Jonathan Vassil on March 13, 2026, indicating the trades were pre-arranged under that plan.
How many Toast (TOST) stock options does Jonathan Vassil retain after these transactions?
After exercising options for 14,280 shares, Vassil directly held 285,871 stock options on Toast Class A Common Stock as of September 2, 2026. The filing notes that the shares subject to this option were fully vested and exercisable.
AI-generated analysis. How Rhea-AI works. Not financial advice.
